The following description includes information that may be useful in understanding the present invention. It is not an admission that any of the information provided herein is prior art or relevant to the presently claimed invention, or that any publication specifically or implicitly referenced is prior art.
As renewable sources, vegetable seed oils are an attractive and environmentally friendly source of long chain hydrocarbon compounds. As a biological source, however, the compounds represented in such vegetable seed oils, while diverse, may not include species that are suited for a desired purpose. Towards that end a variety of methods have been developed to alter the composition of vegetable seed oils. Ideally, such methods should produce desirable compounds, for example oxygenated species such as aldehydes, in useful quantities and in a scalable fashion, and preferably not involve the addition of compounds that would be retained in the product mixture.
Soriano Jr. et al (Electrochemica Acta 50:1131-1137 (2005)) reported production of oxygenated species in sunflower oil via production of trioxilanes by treatment with ozone and low voltage electrolytic reduction. This process, however, required the addition of soluble metal salt electrolytes and alcohol and carboxylic acid proton donors. Similarly, U.S. Pat. No. 7,497,939 (to Matsumura et al) discloses a method for producing oxygenated species from vegetable oil by first esterifying the vegetable oil by treatment with an alcohol and a strong base, then reacting with ozone and performing an electrochemical reduction at low voltage and in the presence of a soluble metal salt electrolyte and organic acid and/or alcohol proton donors. U.S. Pat. No. 6,768,029 (to Khan et al) teaches a method for producing oxygen containing species from various naturally occurring oils by first dissolving the oil in an alcohol and treating with ozone, then performing a chemical reduction using an added reducing sugar (for example, glucose). All of these approaches, however, require the addition of metal salts, organic acids, and/or alcohols that often need to be removed via additional processing steps prior to use of the modified vegetable oil. Such post-reaction processing is a significant impediment to scale-up and commercialization of such methods. The reliance on ozone, which has a permissible exposure limit of 0.1 μmol/mol under current OSHA regulations can also complicate the implementation of such processes.
All publications identified herein are incorporated by reference to the same extent as if each individual publication or patent application were specifically and individually indicated to be incorporated by reference. Where a definition or use of a term in an incorporated reference is inconsistent or contrary to the definition of that term provided herein, the definition of that term provided herein applies and the definition of that term in the reference does not apply.
Thus, there is still a need for a scalable method for generating oxygenated and other useful molecular species from vegetable oils.